It's fascinating how big a quotient the persuasiveness of his speech lies on the vocal level, and is almost nonexistent when written out, abstracting away that detail. It almost makes me think that the current level of chatbots are enough, if only they could nail the text-to-speech component; to really surf whatever it is that makes speech sound powerful and influencial.
The thing is, that's a very hard problem. He's probably got either the luck to be in a favorable space or some sort of native intuition that makes his speeches resonate with a certain group of people.
It's basically something very fuzzy, historically the hardest thing to emulate with computers :)
Fuzzy would imply it's hard or impossible to model it, mathematically. But ask any good biologist and I bet you'll hear quite a bit of confidence that the keys behind powerful speech can be understood. For an engineer without domain expertize, yes it's fuzzy. Armed with the right research papers? Highly likely something persuasive could be implemented.
I'm pretty right leaning and I honestly think the funniest thing is listening to him talk, I never have any idea what he's talking about no matter how long I listen to his speeches. Ideologically he and I agree on some things, but I just never know because I can't understand a single thing he says unless he tweets it. I think he actually suffered when twitter upped the char allowance bec the brevity forced him to be succinct.